Condensed cyclic compounds and organic light-emitting devices including the same

ABSTRACT

A condensed cyclic compound and an organic light-emitting device including the same, the condensed cyclic compound being represented by Formula 1 below:

CROSS-REFERENCE TO RELATED APPLICATION

Korean Patent Application No. 10-2014-0067062, filed on Jun. 2, 2014, in the Korean Intellectual Property Office, and entitled: “Condensed Cyclic Compounds and Organic Light-Emitting Devices Including the Same,” is incorporated by reference herein in its entirety.

BACKGROUND

1. Field

Embodiments relate to condensed cyclic compounds and organic light-emitting devices including the same.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emitting devices that can provide multicolored images and may have advantages such as wide viewing angle, excellent contrast, quick response time, excellent brightness, low driving voltage, and excellent response speed characteristics.

An OLED may have a structure including a first electrode disposed on a substrate, and a hole transport region, an emission layer (EML), an electron transport region, and a second electrode sequentially formed on the first electrode. Holes injected from the first electrode move to the EML via the hole transport region, and electrons injected from the second electrode move to the EML via the electron transport region. Excitons may be generated when carriers such as holes and electrons recombine in the EML. When the excitons drop from an excited state to a ground state, light is emitted.

SUMMARY

Embodiments are directed to condensed cyclic compounds and organic light-emitting devices including the same.

According to one or more embodiments, provided is a condensed cyclic compound represented by Formula 1 below:

in Formula 1,

L₁ to L₄ may be each independently selected from a substituted or unsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstituted C₃-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀ cycloalkenylene group, a substituted or unsubstituted C₃-C₁₀ heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀ arylene group, a substituted or unsubstituted C₂-C₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group;

a1 to a4 may be each independently selected from 0, 1, 2 and 3;

R₁ to R₄ may be each independently selected from hydrogen, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₃-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₃-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group (substituted or unsubstituted monovalent non-aromatic condensed polycyclic group) a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group (substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group), —P(═O)(Q₁)(Q₂), and —S(═O)₂(Q₁);

R₅ to R₇ may be each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀ arythio group, a substituted or unsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group;

b2 to b4 may be each independently selected from 1, 2, 3 and 4;

at least one substituent of the substituted C₃-C₁₀ cycloalkylene group, the substituted C₂-C₁₀ heterocycloalkylene group, the substituted C₃-C₁₀ cycloalkenylene group, the substituted C₂-C₁₀ heterocycloalkenylene group, the substituted C₆-C₆₀ arylene group, the substituted C₂-C₆₀ heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic hetero-condensed polycyclic group, the substituted C₁-C₆₀ alkyl group, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkyl group, the substituted C₂-C₁₀ heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₂-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arythio group, the substituted C₂-C₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed hetero-polycyclic group may be selected from

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arythio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed hetero-polycyclic group;

C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arythio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arythio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed hetero-polycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arythio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group; and

—P(═O)(Q₁₁)(Q₁₂) and —S(═O)₂(Q₁₁); wherein,

Q₁, Q₂, Q₁₁ and Q₁₂ may be each independently selected from a C₆-C₆₀ aryl group, and a C₂-C₆₀ heteroaryl group.

According to another embodiment, provided is an organic light-emitting device including a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, and including an emission layer, wherein the organic layer includes at least one type of condensed cyclic compound.

BRIEF DESCRIPTION OF THE DRAWING

Features will be apparent to those of skill in the art by describing in detail exemplary embodiments with reference to the attached drawings in which:

The FIGURE illustrates a schematic structure of an organic light-emitting device according to an embodiment.

DETAILED DESCRIPTION

Example embodiments will now be described more fully hereinafter with reference to the accompanying drawing; however, they may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey exemplary implementations to those skilled in the art.

In the drawing FIGURE, the dimensions of layers and regions may be exaggerated for clarity of illustration. Like reference numerals refer to like elements throughout.

As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.

The terms used in the present specification are merely used to describe exemplary embodiments, and are not intended to limit the present application. An expression used in the singular encompasses the expression of the plural, unless it has a clearly different meaning in the context.

In the present specification, it is to be understood that the terms such as “including”, “having”, and “comprising” are intended to indicate the existence of the features, numbers, steps, actions, components, parts, or combinations thereof disclosed in the specification, and are not intended to preclude the possibility that one or more other features, numbers, steps, actions, components, parts, or combinations thereof may exist or may be added.

It will be understood that when a layer, region, or component is referred to as being “formed on” another layer, region, or component, it can be directly or indirectly formed on the other layer, region, or component. That is, for example, intervening layers, regions, or components may be present.

The condensed cyclic compound according to an embodiment may be represented by Formula 1 below:

In Formula 1 above, L₁ to L₄ may be each independently selected from a substituted or unsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstituted C₃-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀ cycloalkenylene group, a substituted or unsubstituted C₃-C₁₀ heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀ arylene group, a substituted or unsubstituted C₂-C₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group;

at least one substituent of the substituted C₃-C₁₀ cycloalkylene group, the substituted C₂-C₁₀ heterocycloalkylene group, the substituted C₃-C₁₀ cycloalkenylene group, the substituted C₂-C₁₀ heterocycloalkenylene group, the substituted C₆-C₆₀ arylene group, the substituted C₂-C₆₀ heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, and the substituted divalent non-aromatic hetero-condensed polycyclic group may be selected from

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group and a C₁-C₆₀ alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arythio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arythio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arythio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arythio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group; and

—(═O)(Q₁₁)(Q₁₂) and —S(═O)₂(Q₁₁); wherein,

Q₁₁ and Q₁₂ may be each independently selected from a C₆-C₆₀ aryl group and a C₂-C₆₀ heteroaryl group.

For example, in Formula 1 above, L₁ to L₄ may be each independently a group selected from phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, ovalenylene, pyrrolylene, thiophenylene, furanylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isooxazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene, indolylene, indazolylene, purinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, carbazolylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzoimidazolylene, benzofuranylene, benzothiophenylene, isobenzothiazolylene, benzooxazolylene, isobenzooxazolylene, triazolylene, tetrazolylene, oxadiazolylene, triazinylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, and dibenzocarbazolylene; and

phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, ovalenylene, pyrrolylene, thiophenylene, furanylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isooxazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene, indolylene, indazolylene, purinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, carbazolylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzoimidazolylene, benzofuranylene, benzothiophenylene, isobenzothiazolylene, benzooxazolylene, isobenzooxazolylene, triazolylene, tetrazolylene, oxadiazolylene, triazinylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, and dibenzocarbazolylene, each substituted with at least one group selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, and imidazopyridinyl, but they are not limited thereto.

In an implementation, in Formula 1, L₁ to L₄ may be each independently groups represented by any one of Formulae 3-1 to 3-30, but they are not limited thereto:

in Formulae 3-1 to 3-30,

Y₁ may be O, S, a C(Z₃)(Z₄), N(Z₅), or Si(Z₆)(Z₇);

Z₁ to Z₇ may be each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group,

d1 may be an integer of 1 to 4;

d2 may be an integer of 1 to 3;

d3 may be an integer of 1 to 6;

d4 may be an integer of 1 to 8;

d5 may be 1 or 2; and

d6 may be an integer of 1 to 5. * and *′ may be binding sites to neighboring atoms.

In an implementation, in Formula 1, L₁ to L₄ may be each independently groups selected from Formulae 4-1 to 4-21 below, but they are not limited thereto:

in Formulae 4-1 to 4-21, * and *′ may be binding sites to neighboring atoms.

In Formula 1, a1 represents the number of L₁s and may be selected from 0, 1, 2, and 3. For example, in Formula 1, a1 may be selected from 0, 1, and 2, but it is not limited thereto. When a1 is an integer that is 2 or greater, a plurality of L₁s may be different from or the same as each other. When a1 is 0, (L₁)_(a1) represents a direct bonding.

In Formula 1, a2 represents the number of L₂s and may be selected from 0, 1, 2, and 3. For example, in Formula 1, a2 may be selected from 0, 1, and 2, but it is not limited thereto. According to another embodiment, in Formula 1, a2 may be 0, but it is not limited thereto. When a2 is an integer that is 2 or greater, a plurality of L₂s may be the same as or different from each other. When a2 is 0, (L₂)_(a2) represents direct bonding.

In Formula 1, a3 represents the number of L₃s, and may be selected from 0, 1, 2, and 3. For example, in Formula 1, a3 may be selected from 0, 1, and 2, but it is not limited thereto. According to another embodiment, in Formula 1, a3 may be 0, but it is not limited thereto. When a3 is an integer of 2 or greater, a plurality of L₃s may be the same as or different from each other. When a3 is 0, (L₃)_(a3) represents a direct bonding.

In Formula 1, a4 represents the number of L₄s, and may be selected from 0, 1, 2, and 3. For example, in Formula 1, a4 may be selected from 0, 1, and 2, but it is not limited thereto. According to another embodiment, in Formula 1, a4 may be 0, but it is not limited thereto. When a4 is an integer of 2 or greater, a plurality of L₄s may be the same as or different from each other. When a4 is 0, (L₄)_(a4) represents a direct bonding.

In Formula 1, R₁ to R₄ may be each independently selected from hydrogen, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₃-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₃-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group, —P(═O)(Q₁)(Q₂), and —S(═O)₂(Q₁);

at least one substituent of the substituted C₃-C₁₀ cycloalkyl group, the substituted C₂-C₁₀ heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₂-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, the substituted C₂-C₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed hetero-polycyclic group may be selected from

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group and a C₁-C₆₀ alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arythio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arythio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arythio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed hetero-polycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arythio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group; and

—P(═O)(Q₁₁)(Q₁₂) and —S(═O)₂(Q₁₁); wherein,

Q₁, Q₂, Q₁₁ and Q₁₂ may be each independently selected from a C₆-C₆₀ aryl group, and a C₂-C₆₀ heteroaryl group.

In an implementation, in Formula 1, R₁ to R₄ may be each independently groups selected from hydrogen, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, carbazolyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, a dibenzosilolyl group, benzocarbazolyl, dibenzocarbazolyl, and benzoxanthenyl, —P(═O)(Q₁)(Q₂), and —S(═O)₂(Q₁); and

phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, carbazolyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, a dibenzosilolyl group, benzocarbazolyl, dibenzocarbazolyl, and benzoxanthenyl, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀ alkyl, a C₁-C₂₀ alkoxy, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, carbazolyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, and dibenzocarbazolyl; and

Q₁ and Q₂ may be each independently selected from a C₆-C₆₀ aryl group, but they are not limited thereto.

In an implementation, in Formula 1, R₁ to R₄ may be each independently groups selected from hydrogen, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, chrysenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl quinolinyl, isoquinolinyl, carbazolyl, phenanthrolinyl, benzoimidazolyl, triazinyl, benzoxanthenyl, —P(═O)(Q₁)(Q₂), and —S(═O)₂(Q₁); and

phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, chrysenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl quinolinyl, isoquinolinyl, carbazolyl, phenanthrolinyl, benzoimidazolyl, triazinyl and benzoxanthenyl, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a nitro group, methyl, ethyl, n-propyl, tert-butyl, methoxy, ethoxy, tert-butoxy, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, carbazolyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, and dibenzocarbazolyl; and

Q₁ and Q₂ may be each independently selected from a phenyl group and a naphthyl group, but they are not limited thereto.

In an implementation, in Formula 1, R₁ to R₄ may be each independently selected from hydrogen, —P(═O)(Ph)₂ and —S(═O)₂(Ph) and a group represented by any one of Formulae 5-1 to 5-44, but they are not limited thereto:

in Formulae 5-1 to 5-44, * is a binding site to neighboring atoms.

In Formula 1, R₅ to R₇ may be each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀ arythio group, a substituted or unsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group;

at least one substituent of the substituted C₁-C₆₀ alkyl group, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkyl group, the substituted C₂-C₁₀ heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₂-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arythio group, the substituted C₂-C₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed hetero-polycyclic group may be selected from

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arythio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arythio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group; and

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arythio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed hetero-polycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arythio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group, but they are not limited thereto.

For example, in Formula 1, R₅ to R₇ may be each independently groups selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl, a C₁-C₂₀ alkoxy, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, carbazolyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilolyl, benzocarbazolyl, dibenzocarbazolyl, and benzoxanthenyl; and

phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, carbazolyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl dibenzofuranyl, dibenzothiophenyl, a dibenzosilolyl group, benzocarbazolyl, dibenzocarbazolyl and benzoxanthenyl, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀ alkyl, a C₁-C₂₀ alkoxy, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, carbazolyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, and dibenzocarbazolyl, but they are not limited thereto.

According to another embodiment, in Formula 1, R₅ to R₇ may be each independently groups selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, methyl, ethyl, n-propyl, tert-butyl, methoxy, ethoxy, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, chrysenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl quinolinyl, isoquinolinyl, carbazolyl, phenanthrolinyl, benzoimidazolyl, triazinyl, and benzoxanthenyl; and

phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, chrysenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl quinolinyl, isoquinolinyl, carbazolyl, phenanthrolinyl, benzoimidazolyl, triazinyl and benzoxanthenyl, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a nitro group, methyl, ethyl, n-propyl, tert-butyl, methoxy, ethoxy, tert-butoxy, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, carbazolyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, and dibenzocarbazolyl.

According to another embodiment, in Formula 1, R₅ to R₇ may be each independently selected from hydrogen, deuterium, a cyano group, a nitro group and a group represented by any one of Formulae 5-1 to 5-44 below, but they are not limited thereto:

in Formulae 5-1 to 5-44, * is a binding site to neighboring atoms.

In Formula 1, b5 represents the number of R₅s and may be selected from 1, 2, and 3. When b5 is an integer of 2 or greater, a plurality of R₅s may be the same or different.

In Formula 1, b6 represents the number of R₆s and may be selected from 1, 2, and 3. When b6 is an integer of 2 or greater, a plurality of R₆s may be the same or different from each other.

In Formula 1, b7 represents the number of R₇s, and may be selected from 1, 2, and 3. When b7 is an integer of 2 or greater, a plurality of R₇s may be the same as or different from each other.

According to an embodiment, the condensed cyclic compound, e.g., represented by Formula 1, may be represented by any one of Formulae 1A to 1D, but they are not limited thereto.

In Formulae 1A to 1D, descriptions of L₁ to L₄, a1 to a4, R₁ to R₇, and b5 to b7 may be the same as described above, e.g., as described with respect to Formula 1.

According to another embodiment, the condensed cyclic compound, e.g., represented by Formula 1, may be represented by any one of Formulae 1E to 1H, but they are not limited thereto.

in Formulae 1E to 1H, descriptions of L₁ to L₄, a1 to a4 and R₁ to R₄ may be the same as described above, e.g., with respect to Formula 1.

When the condensed cyclic compound is represented by any one of Formulae 1E to 1H, L₁ to L₄ may be each independently selected from groups represented by Formulae 4-1 to 4-21, and a1 may be selected from 0, 1, and 2, but they are not limited thereto.

When the condensed cyclic compound is represented by any one of Formulae 1E to 1H, R₁ to R₄ may be each independently selected from hydrogen and any one of groups represented by Formulae 5-1 to 5-44, but they are not limited thereto.

According to another embodiment, the condensed cyclic compound, e.g., represented by Formula 1, may be selected from Compounds 1 to 82 below, but they are not limited thereto.

An organic light-emitting device including the condensed cyclic compound represented by Formula 1 above may have low driving voltage, high efficiency, high brightness, and long lifespan.

The condensed cyclic compound represented by Formula 1 above may be synthesized by using a suitable organic synthesis method. The method of synthesizing the condensed cyclic compound may be understood based on the embodiments described below.

The condensed cyclic compound represented by Formula 1 above may be used between a pair of electrodes in an organic light-emitting device. For example, the condensed cyclic compound may be included in an electron transport layer (ETL). Accordingly, provided is an organic light-emitting device including a first electrode, a second electrode disposed opposite to the first electrode, an organic layer disposed between the first electrode and the second electrode and including an emission layer (EML), wherein, the organic layer includes at least one type of condensed cyclic compound represented by Formula 1 described above.

As used herein, the expression “(organic layer) includes at least one of a first material” may be construed as “(organic layer) may include one of a first material in a range of Formula 1 or two or more different first materials in the range of Formula 1”.

For example, the organic layer may only include Compound 1 as the condensed cyclic compound. In this regard, Compound 1 may only exist in the ETL or the organic light-emitting device. Alternatively, the organic layer may include Compound 1 and Compound 2 as the condensed cyclic compound. In this regard, Compound 1 and Compound 2 may exist in the same layer (for example, Compound 1 and Compound 2 may both exist in the ETL) or in different layers (for example, Compound 1 may only exist in the EML and Compound 2 may only exist in the ETL).

The organic layer include i) a hole transport region disposed between the first electrode and the emission layer (EML) and including at least one selected from a hole injection layer (HIL), a hole transport layer (HTL), a buffer layer, and an electron blocking layer (EBL); and ii) an electron transport region disposed between the EML and the second electrode and including at least one selected from a hole blocking layer (HBL), an ETL, and an EIL.

As used herein, the expression, the “organic layer” is a term that refers to a single layer and/or a multi-layer disposed between the first electrode and the second electrode in the organic light-emitting device. Materials included in the “organic layer” are not limited to organic materials.

The FIGURE schematically illustrates a structure of an organic light-emitting device according to an embodiment. The organic light-emitting device 10 may include a first electrode 110, an organic layer 150, and a second electrode 190.

Hereinafter, a structure and a method of manufacturing an organic light-emitting device according to an embodiment will be described with reference to the FIGURE.

A substrate may be additionally disposed under the first electrode 110 or on the second electrode 190 in the FIGURE. The substrate may be a glass substrate or a transparent plastic substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

The first electrode 110 may be formed by, for example, depositing or sputtering a material for a first electrode 110 on the substrate. When the first electrode 110 is an anode, the material for the first electrode 110 may be selected from materials with a high work function to enable ease of hole injection. The first electrode 110 may be a reflective electrode, a semi-transmission electrode, or a transmission electrode. The material for the first electrode 110 may be a transparent material with high conductivity, and examples of such a material are indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), and zinc oxide (ZnO). To manufacture the first electrode 110, which is a semi-transmission electrode or a transmission electrode, at least one of magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or the like may be used.

The first electrode 110 may have a single-layer structure or a multi-layer structure including a plurality of layers. For example, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO, but is not limited thereto.

The organic layer 150 may be disposed on the first electrode 110. The organic layer 150 includes an EML.

The organic layer 150 may further include a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode.

The hole transport region may include at least one selected from a HIL, a HTL, a buffer layer, and an EBL and the electron transport region may include at least one selected from a HBL, an ETL, and an EIL, but they are not limited thereto.

The hole transport region may include a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multi-layered structure including a plurality of layers formed of a plurality of different materials.

For example, the ole transport region may have a single-layered structure formed of a plurality of different materials or a structure in which HIL/HTL, HIL/HTL/buffer layer, HIL/buffer layer, HTL/buffer layer, or HIL/HTL/EBL are sequentially layered on the first electrode 110, but it is not limited thereto.

When the hole transport region includes the HIL, the HIL may be formed on the first electrode 110 by using various methods, such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).

When the HIL is formed by using vacuum deposition, vacuum deposition conditions may vary according to the compound that is used to form the HIL and the desired structure of the HIL to be formed. For example, vacuum deposition may be performed at a temperature of about 100° C. to about 500° C., a pressure of about 10⁻⁸ torr to about 10⁻³ torr, and a deposition rate of about 0.01 to about 100 Å/sec, depending on the structure of the HIL to be formed.

When the HIL is formed by using spin coating, the coating conditions may vary according to the compound that is used to form the HIL and the desired structure of the HIL to be formed. For example, the coating rate may be in the range of about 2000 rpm to about 5000 rpm, and a temperature at which a heat treatment is performed may be in the range of about 80° C. to about 200° C.

When the hole transport region includes the HTL, the HTL may be formed on the first electrode 110 or on the HIL by using various methods, such as vacuum deposition, spin coating, casting, LB deposition, inkjet printing, laser printing, and LITI. When the HTL is formed by vacuum deposition or spin coating, vacuum deposition conditions and coating conditions may be the same as the vacuum deposition conditions and the coating conditions of the HIL.

The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NBP, β-NPD, TPD, Spiro-TPD, Spiro-NPB, α-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(4,4′,4″-tris(N-carbazolyl)triphenylamine) (TCTA), polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (pani/CSA), (polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201 below, and a compound represented by Formula 202 below.

in Formulae 201 and 202,

descriptions of L₂₀₁ to L₂₀₅ may be each independently understood by referring to the description of L₁ as described above;

xa1 to xa4 may be each independently selected from 0, 1, 2, and 3;

xa5 may be selected from 1, 2, 3, 4, and 5;

descriptions of R₂₀₁ to R₂₀₅ may be each independently understood by referring to the description of R₁.

For example, in Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may be each independently selected from a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, benzofluorene group, dibenzofluorene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group and a triazinylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;

xa1 to xa4 may be each independently selected from 0, 1, or 2; and

xa5 may be 1, 2, or 3;

R₂₀₁ to R₂₀₅ may be each independently selected from a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, an azulenyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group, but they are not limited thereto.

The compound represented by Formula 201 above may be represented by Formula 201A below:

For example, the compound represented by Formula 201 above may be represented by Formula 201A-1 below, but it is not limited thereto:

The compound represented by Formula 202 above may be represented by Formula 202A below, but it is not limited thereto:

In Formulae 201A, 201A-1, and 202A, descriptions of L₂₀₁ to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂ to R₂₀₄ may be understood by referring to the descriptions above, R₂₁₁ may be understood by referring to the description of R₂₀₃, and R₂₁₃ to R₂₁₆ may be each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arythio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group.

For example, in Formulae 201A, 201A-1, and 202A,

L₂₀₁ to L₂₀₃ may be each independently selected from a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group and a triazinylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;

xa1 to xa3 may be each independently 0 or 1;

R₂₀₃, R₂₁₁ and R₂₁₂ may be each independently selected from a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group;

R₂₁₃ and R₂₁₄ may be ach independently selected from C₁-C₂₀ alkyl and a C₁-C₂₀ alkoxy;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;

R₂₁₅ and R₂₁₆ may be each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a slat thereof, phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl and a C₁-C₂₀ alkoxy, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

xa5 may be 1 or 2.

In Formulae 201A and 201A-1 above, R₂₁₃ and R₂₁₄ may bind to each other to form a saturated ring or an unsaturated ring.

The compound represented by Formula 201 above and the compound represented by Formula 202 above may include Compounds HT1 to HT20, but they are not limited thereto.

A thickness of the hole transport region may be about 100 Å to about 10,000 Å, for example about 100 Å to about 1,000 Å. When the hole transport region includes both of the HIL and the HTL, a thickness of the HIL may be about 100 Å to about 10000 Å, for example, about 100 Å to about 1,000 Å and a thickness of the HTL may be about 50 Å to about 2,000 Å, for example, about 100 Å to about 1500 Å. When the thickness of the hole transport region, the HIL, and the HTL satisfy the ranges described above, satisfactory hole injection characteristics may be obtained without a substantial increase in a driving voltage.

The hole transport region may further include a charge-generating material, in addition to the material described above. The charge-generating material may be uniformly or disuniformly dispersed in the hole transport region.

The charge-generating material may be, for example, a p-dopant. The p-dopant may be selected from quinone derivatives, metal oxides, and CN-containing compounds, but it is no limited thereto. For example, non-limiting examples of the p-dopant are quinone derivatives, such as tetracyanoquinodimethane (TCNQ), and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); metal oxides such as tungsten oxides and molybdenym oxides; and Compound HT-D1 below.

The hole transport region may include at least one selected from the buffer layer and the EBL, in addition to the HIL and the HTL. The buffer layer may compensate for an optical resonance distance of light according to a wavelength of the light emitted from the emission layer (EML), and thus may increase efficiency of light emission. The buffer layer may include any material that may be used in the hole transport region. The EBL may prevent injection of electrons from the electron transport region.

Then, the EML may be formed on the first electrode 110 or the hole transport region by vacuum deposition, spin coating, casting, LB deposition, inkjet printing, laser printing, LITI, or the like. When the EML is formed using vacuum deposition or spin coating, the deposition and coating conditions may be similar to those for the formation of the HIL.

When the organic light-emitting device 10 is a full color organic light-emitting device, the organic light-emitting device 10 may be patterned into red EML, green EML, and blue EML, according to different EMLs and the individual sub-pixels. Alternatively, the EML may have a structure in which the red EML, the green EML, and the blue EML are layered or a structure in which a red light emission material, a green light emission material, and a blue light emission material are mixed without separation of layers and emit white light. Alternatively, the EML is a white light EML, which includes a color filter or a color converting layer that converts white light into light of desired color.

The EML may include a host and a dopant.

The host may include at least one selected from TPBi, TBADN, ADN (also known as “DNA”), CBP, CDBP, and TCP:

In an implementation, the host may include a compound represented by Formula 301 below. Ar₃₀₁-[(L₃₀₁)_(xb1)-R₃₀₁]_(xb2)  <Formula 301>

in Formula 301,

Ar₃₀₁ may be selected from naphthalene, heptalene, fluorene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, and indenoanthracene;

naphthalene, heptalene, fluorene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene and indenoanthracene, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arythio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed hetero-polycyclic group and —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃) (wherein, Q₃₀₁ to Q₃₀₃ may be each independently selected from hydrogen, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₆-C₆₀ aryl group, and a C₂-C₆₀ heteroaryl group);

description of L₃₀₁ may be understood by referring to the description of L₂₀₁;

R₃₀₁ may be selected from a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazole group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazole group, and a triazinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group;

xb1 may be selected from 0, 1, 2, and 3; and

xb2 may be selected from 1, 2, 3, and 4.

For example, in Formula 301 above,

L₃₀₁ may be selected from a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, and a chrysenylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, and a chrysenylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group;

R₃₀₁ may be selected from a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group and a chrysenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group, but it is not limited thereto.

For example, the host may include a compound represented by Formula 301A below:

In Formula 301A above, descriptions of the substituents may be understood by referring to the descriptions herein.

The compound represented by Formula 301 above may include at least one selected from Compounds H1 to H42, but it is not limited thereto.

In an implementation, the host may include at least one selected from Compounds H43 to H49 below, but is not limited thereto.

The dopant may further include at least one of a fluorescent dopant and a phosphorescent dopant.

The phosphorescent dopant may include an organic metal, e.g., organometallic, complex represented by Formula 401 below:

in Formula 401,

M may be selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm);

X₄₀₁ to X₄₀₄ may be each independently selected from nitrogen or carbon;

A₄₀₁ and A₄₀₂ rings may be each independently selected from a substituted or unsubstituted benzene, a substituted or unsubstituted naphthalene, a substituted or unsubstituted fluorene, a substituted or unsubstituted spiro-fluorene, a substituted or unsubstituted indene, a substituted or unsubstituted pyrrol, a substituted or unsubstituted thiophene, a substituted or unsubstituted furan, a substituted or unsubstituted imidazole, a substituted or unsubstituted pyrazole, a substituted or unsubstituted thiazole, a substituted or unsubstituted isothiazole, a substituted or unsubstituted oxazole, a substituted or unsubstituted isooxazole, a substituted or unsubstituted pyridine, a substituted or unsubstituted pyrazine, a substituted or unsubstituted pyrimidine, a substituted or unsubstituted, pyridazine, a substituted or unsubstituted quinoline, a substituted or unsubstituted isoquinoline, a substituted or unsubstituted benzoquinoline, a substituted or unsubstituted quinoxaline, a substituted or unsubstituted quinazoline, a substituted or unsubstituted carbazole, a substituted or unsubstituted benzoimidazole, a substituted or unsubstituted benzofuran, a substituted or unsubstituted benzothiophene, a substituted or unsubstituted isobenzothiophene, a substituted or unsubstituted benzooxazole, a substituted or unsubstituted isobenzooxazole, a substituted or unsubstituted triazole, a substituted or unsubstituted oxadiazole, a substituted or unsubstituted triazine, a substituted or unsubstituted dibenzofuran, and a substituted or unsubstituted dibenzothiophene;

at least one substituent of the substituted benzene, substituted naphthalene, substituted fluorene, substituted spiro-fluorene, substituted indene, substituted pyrrol, substituted thiophene, substituted furan, substituted imidazole, substituted pyrazole, substituted thiazole, substituted isothiazole, substituted oxazole, substituted isooxazole, substituted pyridine, substituted pyrazine, substituted pyrimidine, substituted pyridazine, substituted quinoline, substituted isoquinoline, substituted benzoquinoline, substituted quinoxaline, substituted quinazoline, substituted carbazole, substituted benzoimidazole, substituted benzofuran, substituted benzothiophene, substituted isobenzothiophene, substituted benzooxazole, substituted isobenzooxazole, substituted triazole, substituted oxadiazole, substituted triazine, substituted dibenzofuran and substituted dibenzothiophene may be selected from

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl, a C₂-C₆₀ alkenyl, a C₂-C₆₀ alkynyl, and a C₁-C₆₀ alkoxy;

a C₁-C₆₀ alkyl, a C₂-C₆₀ alkenyl, a C₂-C₆₀alkynyl and a C₁-C₆₀ alkoxy, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₃-C₁₀cycloalkyl, a C₃-C₁₀ heterocycloalkyl, a C₃-C₁₀cycloalkenyl, a C₃-C₁₀ heterocycloalkenyl, a C₆-C₆₀aryl, a C₆-C₆₀ aryloxy, a C₆-C₆₀ arylthio, a C₂-C₆₀ heteroaryl, non-aromatic condensed polycyclic group (non-aromatic condensed polycyclic group), —N(Q₄₀₁)(Q₄₀₂), —Si(Q₄₀₃)(Q₄₀₄)(Q₄₀₅), and —B(Q₄₀₆)(Q₄₀₇);

a C₃-C₁₀ cycloalkyl, a C₃-C₁₀ heterocycloalkyl, a C₃-C₁₀ cycloalkenyl, a C₃-C₁₀ heterocycloalkenyl, a C₆-C₆₀ aryl, a C₆-C₆₀ aryloxy, a C₆-C₆₀ arylthio, a C₂-C₆₀ heteroaryl, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero condensed polycyclic group;

a C₃-C₁₀cycloalkyl, a C₃-C₁₀ heterocycloalkyl, a C₃-C₁₀cycloalkenyl, a C₃-C₁₀ heterocycloalkenyl, a C₆-C₆₀aryl, a C₆-C₆₀ aryloxy, a C₆-C₆₀ arylthio, a C₂-C₆₀ heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic hetero condensed polycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl, a C₂-C₆₀ alkenyl, a C₂-C₆₀ alkynyl, a C₁-C₆₀ alkoxy, a C₃-C₁₀cycloalkyl, a C₃-C₁₀ heterocycloalkyl, a C₃-C₁₀cycloalkenyl, a C₃-C₁₀ heterocycloalkenyl, a C₆-C₆₀ aryloxy, a C₆-C₆₀ arylthio, a C₂-C₆₀ heteroaryl, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic hetero condensed polycyclic group, —N(Q₄₁₁)(Q₄₁₂), —Si(Q₄₁₃)(Q₄₁₄)(Q₄₁₅), and —B(Q₄₁₆)(Q₄₁₇); and

—N(Q₄₂₁)(Q₄₂₂), —Si(Q₄₂₃)(Q₄₂₄)(Q₄₂₅) and —B(Q₄₂₆)(Q₄₂₇);

L₄₀₁ is an organic ligand;

xc1 is 1, 2, or 3; and

xc2 is 0, 1, 2, or 3.

L₄₀₁ may be any of a monovalent, a divalent, or a trivalent organic ligand. For example, L₄₀₁ may be selected from a halogen ligand (for example, Cl and F), a diketone ligand (for example, acetylacetonate, 1,3-diphenyl-1,3-propanedionate, 2,2,6,6-tetramethyl-3,5-heptanedionate, and hexafluoroacetonate), a carboxylic acid ligand (for example, picolinate, dimethyl-3-pyrazolecarboxylate, and benzoate), a carbon monoxide ligand, an isonitrile ligand, a cyano ligand, and a phosphorous ligand (for example, phosphine), phosphaite, but it is not limited thereto.

In Formula 401, when A₄₀₁ has two or more substituents, the two or more substituents of A₄₀₁ may be bound to each other to form a saturated ring or an unsaturated ring.

In Formula 401, when A₄₀₂ has two or more substituents, the two or more substituents of A₄₀₂ may be bound to each other to form a saturated ring or an unsaturated ring.

In Formula 401, when xc1 is two or greater, a plurality of ligands in Formula 401

may be the same as or different from each other. In Formula 401, when xc1 is two or greater, each of A₄₀₁ and A₄₀₂ may be connected to each of A₄₀₁ and A₄₀₂ of a neighboring ligand either directly or via a linking group (for example, a C₁-C₅ alkylene and —N(R′)— (wherein, R′ is a C₁-C₁₀ alkyl group or a C₆-C₂₀ aryl group), or —C(═O)—).

The phosphorescent dopant may include at least one of Compounds PD1 to PD74, but it is not limited thereto.

In an implementation, the phosphorescent dopant may include PtOEP below:

The fluorescent dopant may include at least one selected from DPAVBi, BDAVBi, TBPe, DCM, DCJTB, Coumarin 6, and C545T.

In an implementation, the fluorescent dopant may include a compound represented by Formula 501 below:

in Formula 501,

Ar₅₀₁ may be selected from naphthalene, heptalene, fluorene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, and indenoanthracene;

naphthalene, heptalene, fluorene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene and indenoanthracene, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl, a C₂-C₆₀alkenyl, a C₂-C₆₀alkynyl, a C₁-C₆₀ alkoxy, a C₃-C₁₀cycloalkyl, a C₃-C₁₀ heterocycloalkyl, a C₃-C₁₀cycloalkenyl, a C₃-C₁₀ heterocycloalkenyl, a C₆-C₆₀aryl, a C₆-C₆₀ aryloxy, a C₆-C₆₀ arylthio, a C₂-C₆₀ heteroaryl, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed hetero-polycyclic group, and —Si(Q₅₀₁)(Q₅₀₂)(Q₅₀₃) (wherein, Q₅₀₁ to Q₅₀₃ may be each independently selected from hydrogen, a C₁-C₆₀ alkyl, a C₂-C₆₀ alkenyl, a C₆-C₆₀ aryl and a C₂-C₆₀ heteroaryl);

descriptions of L₅₀₁ to L₅₀₃ may be understood by referring to the description of L₂₀₁ herein;

R₅₀₁ and R₅₀₂ may be each independently selected from phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazole, triazinyl, dibenzofuranyland dibenzthiophenyl; and

phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl and dibenzofuranyland dibenzothiophenyl, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl, a C₁-C₂₀ alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, dibenzofuranyl, and dibenzothiophenyl;

xd1 to xd3 may be each independently selected from 0, 1, 2, and 3; and

xb4 may be selected from 1, 2, 3, and 4.

The fluorescent dopant may include at least one selected from Compounds FD1 to FD8:

In the EML, an amount of the dopant may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but it is not limited thereto.

A thickness of the EML may be about 100 Å to about 1000 Å, for example, about 200 Å to about 600 Å. When the thickness of the EML is in the range described above, the EML may have excellent light-emitting ability without a substantial increase in driving voltage.

The electron transport region may be disposed on the EML.

The electron transport region may include at least one of the HBL, the ETL, and EIL, but it is not limited thereto.

For example, the electron transport region may have a structure in which the ETL, the ETL/EIL or HBL/ETL/EIL is sequentially layered on the EML, but it is not limited thereto.

The electron transport region may include an HBL. When the EML includes a phosphorescent dopant, the HBL may be formed to prevent diffusion of triplet excitons or holes into the ETL.

When the electron transport region includes the HBL, the HBL may be formed on the EML by using various methods such as vacuum deposition, spin coating, casting, LB, inkjet printing, laser printing, and LITI. When the HBL is formed by vacuum deposition and spin coating, the deposition and coating conditions may be similar to those for forming the HIL, though the deposition and coating conditions may vary according to a compound that is used to form the HBL.

The HBL may include at least one of BCP and Bphen, but it is not limited thereto.

A thickness of the HBL may be from about 20 Å to about 1,000 Å, and in some embodiments, may be from about 30 Å to about 300 Å. When the thickness of the HBL is within these ranges, the HBL may have a hole blocking transporting ability without a substantial increase in driving voltage.

The electron transport region may include an ETL. The ETL may be formed on the EML or the HBL by using various methods such as vacuum deposition, spin coating, casting, LB, inkjet printing, laser printing, and LITI. When the ETL is formed by vacuum deposition and spin coating, the deposition and coating conditions may be similar to those for forming the HIL, though the deposition and coating conditions may vary according to a compound that is used to form the ETL.

The ETL may include the condensed cyclic compound represented by Formula 1 above.

The ETL may include at least ne of BCP, Bphen above the Alq₃, Balq, TAZ and NTAZ below, in addition to the condensed cyclic compound represented by Formula 1 above.

In an implementation, the ETL may include the condensed cyclic compound represented by Formula 1 above along with a compound represented by Formula 601 below: Ar₆₀₁-[L₆₀₁)_(xe1)-E₆₀₁]_(xe2)  <Formula 601>

in Formula 601,

Ar₆₀₁ may be selected from naphthalene, heptalene, fluorene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, and indenoanthracene; and

naphthalene, heptalene, fluorene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene and indenoanthracene, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, C₁-C₆₀ alkyl, C₂-C₆₀ alkenyl, C₂-C₆₀ alkynyl, C₁-C₆₀ alkoxy, C₃-C₁₀ cycloalkyl, C₃-C₁₀ heterocycloalkyl, C₃-C₁₀ cycloalkenyl, C₃-C₁₀ heterocycloalkenyl, C₆-C₆₀ aryl, C₆-C₆₀ aryloxy, C₆-C₆₀ arylthio, C₂-C₆₀ heteroaryl, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed hetero-polycyclic group, and —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃) (wherein, Q₃₀₁ to Q₃₀₃ may be each independently, hydrogen, C₁-C₆₀ alkyl, C₂-C₆₀ alkenyl, C₆-C₆₀ aryl, and C₂-C₆₀ heteroaryl);

description of L₆₀₁ may be understood by referring to the description of L₂₀₁;

E₆₀₁ may be selected from pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, and dibenzocarbazolyl; and

pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl and dibenzocarbazolyl, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, C₁-C₂₀ alkyl, C₁-C₂₀ alkoxy, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, and dibenzocarbazolyl;

xe1 may be selected from 0, 1, 2, and 3; and

xe2 may be selected from 1, 2, 3, and 4.

In an implementation, the ETL may include at least one of the compounds represented by Formula 602:

in Formula 602,

X₆₁₁ may be selected from N or C-(L₆₁₁)_(xe611)-R₆₁₁, X₆₁₂ may be selected from N or C-(L₆₁₂)_(xe612)-R₆₁₂, X₆₁₃ may be selected from N or C-(L₆₁₃)_(xe613)-R₆₁₃, and at least one of X₆₁₁ to X₆₁₃ may be N;

description for each of L₆₁₁ to L₆₁₆ may be understood by referring to the description of L₂₀₁ herein;

R₆₁₁ to R₆₁₆ may be each independently selected from phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, and triazinyl; and

phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl, a C₁-C₂₀ alkoxy, phenyl, naphthyl, azulenyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, and triazinyl; and

xe611 to xe616 may be each independently selected from 0, 1, 2, and 3.

The compound represented by Formula 601 and the compound represented by Formula 602 above may include at least one from Compounds ET1 to ET15 below.

A thickness of the ETL may be about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the ETL is within the range described above, the ETL may have satisfactory electron transport characteristics without a substantial increase in driving voltage.

The ETL may further include a metal-containing material in addition to the material described above.

The metal-containing material may include a Li complex. The Li complex may, for example, include compounds ET-D1 (lithium quinolate: LiQ) or ET-D2 illustrated below.

The electron transport region may include and EIL that facilitates electron injection from the second electrode 190.

The EIL may be formed on the ETL by using various methods such as vacuum deposition, spin coating, casting, LB, inkjet printing, laser printing, and LITI. When the EIL is formed by vacuum deposition or spin coating, the deposition and coating conditions may be similar to those for forming the HIL. When the EIL is formed using a vacuum deposition or spin coating, the deposition and coating conditions may be similar to those for the formation of the HIL.

The EIL may include at least one selected from LiF, NaCl, CsF, Li₂O, BaO, and LiQ.

A thickness of the EIL may be about 1 Å to about 100 Å or about 3 Å to about 90 Å. When the thickness of the EIL is within the range described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.

The second electrode 190 is disposed on the organic layer 150 described above. The second electrode 190 may be a cathode, which is an electron injection electrode, in which a material of the second electrode 190 may be a metal, an alloy, an electroconductive compound, or a mixture thereof having a low work function. Detailed examples of the material of the second electrode 190 include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), and magnesium-silver (Mg—Ag). In an implementation ITO, IZO, or the like may be used as the material of the second electrode 190. The second electrode 190 may be a reflective electrode, a semi-transmission electrode, or a transmission electrode.

Hereinabove, the organic light-emitting device is described with reference to the FIGURE, but it is not limited thereto.

As used herein, the C₁-C₆₀ alkyl group refers to a linear or branched aliphatic C₁-C₆₀ hydrocarbon monovalent group and detailed examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group. As used herein, the C₁-C₆₀ alkylene group refers to a divalent group having the same structure as the C₁-C₆₀ alkyl group.

As used herein, the C₁-C₆₀ alkoxy group is a monovalent group having a formula of —OA₁₀₁ (wherein, A₁₀₁ is the C₁-C₆₀ alkyl group) and detailed examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.

As used herein, the C₂-C₆₀ alkenyl group refers to a C₂-C₆₀ alkyl group having one or more carbon-carbon double bonds at a center or end thereof. Examples of the unsubstituted C₂-C₆₀ alkenyl group are en ethenyl group, a propenyl group, and a butenyl group. As used herein, the C₂-C₆₀ alkenylene group refers to a divalent group having the same structure as the C₂-C₆₀ alkenyl group.

As used herein, the C₂-C₆₀ alkynyl group refers to an unsubstituted C₂-C₆₀ alkyl group having one or more carbon-carbon triple bonds at a center or end thereof. Examples of the C₂-C₆₀ alkynyl group are an ethynyl group, a propynyl group, and the like. As used herein, the C₂-C₆₀ alkynylene group refers to a divalent group having the same structure as the C₂-C₆₀ alkynyl group.

As used herein, the C₃-C₁₀ cycloalkyl group refers to a C₃-C₁₀ monovalent hydrocarbon monocyclic group and detailed examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. As used herein, the C₃-C₁₀ cycloalkylene group refers to a divalent group having the same structure as the C₃-C₁₀ cycloalkyl group.

As used herein, the C₂-C₁₀ heterocycloalkyl group refers to a C₂-C₁₀ monovalent monocyclic group including at least one selected from N, O, P, and S as a ring-forming atom and detailed examples thereof include a tetrahydrofuranyl group and a tetrahydrothiophenyl group. As used herein, the C₂-C₁₀ heterocycloalkylene group refers to a divalent group having the same structure as the C₂-C₁₀ heterocycloalkyl group.

As used herein, the C₃-C₁₀ cycloalkenyl group refers to a C₃-C₁₀ monovalent monocyclic group having at least one double bond in a ring but without aromaticity, and detailed examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. As used herein, the C₃-C₁₀ cycloalkenylene group refers to a divalent group having the same structure as the C₃-C₁₀ cycloalkenyl group.

As used herein, the C₂-C₁₀ heterocycloalkenyl group is a C₂-C₁₀ monovalent monocyclic group including at least one selected from N, O, P, and S as a ring-forming atom, and includes at least one double bond in a ring. Detailed examples of the C₂-C₁₀ heterocycloalkenyl group include a 2,3-hydrofuranyl group and a 2,3-hydrothiophenyl group. As used herein, the C₂-C₁₀ heterocycloalkenylene group is a divalent group having the same structure as the C₂-C₁₀ heterocycloalkenyl group.

As used herein, the C₆-C₆₀ aryl group is a C₆-C₆₀ monovalent group having a carbocyclic aromatic system and the C₆-C₆₀ arylene group refers to a divalent group having a C₆-C₆₀ carbocyclic aromatic system. Examples of the C₆-C₆₀ aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylene group include two or more rings, the two or more rings may be fused to each other.

As used herein, the C₂-C₆₀ heteroaryl group refers to a monovalent group having a C₂-C₆₀ carbocyclic aromatic system including at least one heteroatom selected from N, O, P, and S as a ring-forming atom and the C₂-C₆₀ heteroarylene group refers to a divalent group having a C₂-C₆₀ carbocyclic aromatic system including at least one heteroatom selected from N, O, P, and S. Examples of the C₂-C₆₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C₂-C₆₀ heteroaryl group and the C₂-C₆₀ group include two or more rings, the two or more rings may be fused to each other.

As used herein, the C₆-C₆₀ aryloxy group refers to —OA₁₀₂ (wherein, A₁₀₂ is the C₆-C₆₀ aryl group) and the C₆-C₆₀ arythio group refers to —SA₁₀₃ (wherein, A₁₀₃ is the C₆-C₆₀ aryl group).

As used, herein, the monovalent non-aromatic condensed polycyclic group refers to a monovalent group having two or more rings that are fused to each other, including only carbon as a ring forming atom (for example, carbon number may be 8 to 60), wherein the entire molecule does not have aromacity. Examples of the non-aromatic condensed polycyclic group include a fluorenyl group or the like. As used herein, the divalent non-aromatic condensed polycyclic group may refer to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

As used herein, the monovalent non-aromatic hetero-condensed polycyclic group refers to a monovalent group having two or more rings that are fused to each other, including a heteroatom selected from N, O, P, and S as a ring-forming atom, in addition to carbon (for example, carbon number may be 2 to 60), wherein the entire molecule does not have aromaticity. The monovalent non-aromatic hetero-condensed polycyclic group includes a carbazolyl group or the like. As used herein, the divalent non-aromatic hetero-condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic hetero-condensed polycyclic group.

As used herein, at least one substituent of the substituted C₃-C₁₀ cycloalkylene group, substituted C₂-C₁₀ heterocycloalkylene group, substituted C₃-C₁₀ cycloalkenylene group, substituted C₂-C₁₀ heterocycloalkenylene group, substituted C₆-C₆₀ arylene group, substituted C₂-C₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic hetero-condensed polycyclic group, substituted C₁-C₆₀ alkyl group, substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynyl group, substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkyl group, substituted C₂-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀ cycloalkenyl group, substituted C₂-C₁₀ heterocycloalkenyl group, substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group, substituted C₆-C₆₀ arythio group, substituted C₂-C₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed hetero-polycyclic group may be selected from

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group and a C₁-C₆₀ alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cycloheptenyl group, a phenyl group, a pentalenyl, group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl, group, a perylenyl group, pentaa phenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, isoa benzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇);

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cycloheptenyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, pentaa phenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, isoa benzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and an imidazopyridinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cycloheptenyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, pentaa phenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, isoa benzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and an imidazopyridinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a phenyl group, a naphthyl group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇); wherein,

Q₁ to Q₇, Q₁₁ to Q₁₇, Q₂₁ to Q₂₇ and Q₃₁ to Q₃₇ may be each independently selected from hydrogen, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cycloheptenyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, pentaa phenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, isoa benzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and an imidazopyridinyl group.

As used herein, the term “Ph” refers to a phenyl group, the term “Me” refers to a methyl group, the term “Et” refers to an ethyl group, and the term “ter-Bu” or “Bu¹” refers to a tert-butyl group.

Hereinafter, an organic light-emitting device will be described in greater detail with reference to Synthesis Examples and Examples. In Synthesis Examples below, a molar equivalent of A and a molar equivalent of B are the same in the expression “B was used instead of A”.

The following Examples and Comparative Examples are provided in order to highlight characteristics of one or more embodiments, but it will be understood that the Examples and Comparative Examples are not to be construed as limiting the scope of the embodiments, nor are the Comparative Examples to be construed as being outside the scope of the embodiments. Further, it will be understood that the embodiments are not limited to the particular details described in the Examples and Comparative Examples.

EXAMPLE Synthesis Example 1: Synthesis of Compound 2

Synthesis of Intermediate 2-1

2.57 g (10 mmol) of 9-bromophenanthrene was dissolved in 30 mL of THF to prepare a dissolution product, and 4 mL of n-butyllithium (2.5 M in hexane) was added to the dissolution product at a temperature of −78° C. to prepare a mixture. After 1 hour, 2.04 mL (10 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane was added to the mixture at the same temperature. Then, the mixture was stirred at room temperature for 5 hours, water was added thereto, and then a product obtained thereform was washed three times with 30 mL of diethylether. A washed diethylether layer obtained therefrom was dried by using MgSO₄ and then reduced pressure dried to obtain a product, and the product was separated and purified by using silica gel column chromatography to obtain 2.28 g of Intermediate 2-1 as a white solid (yield 75%). The compound produced was identified by using LC-MS. C₂₀H₂₁BO₂: M⁺304.2.

Synthesis of Intermediate 2-2

3.04 g (10.0 mmol) of Intermediate 2-1, 2.02 g (10.0 mmol) of 1-bromo-2-nitrobenzene, 0.58 g (0.5 mmol) of Pd(PPh₃)₄, 0.16 g (0.5 mmol) of tetrabutylammonium bromide (TBAB) and 3.18 g (30.0 mmol) of Na₂CO₃ were dissolved in 60 mL of a mixture solution of toluene/ethanol/H₂O (volume ratio of 3/3/1), and then stirred for 16 hours at a temperature of 80° C. A reaction solution obtained therefrom was cooled to room or ambient temperature and then extracted three times with 60 mL of water and 60 mL of diethylether. An organic layer obtained therefrom was dried with magnesium sulfate and solvents were evaporated therefrom to obtain residues, and the residues were separated and purified by using silica gel column chromatography to obtain 2.39 g of Intermediate 2-2 (yield 80%). The compound produced was identified by using LC-MS. C₂₀H₁₃NO₂: M⁺ 299.1

Synthesis of Intermediate 2-3

2.99 g (10.0 mmol) of Intermediate 2-2, 3.56 g (30 mmol) of tin (Sn), and 5 ml (50 mmol, conc. 36.5%) of hydrochloric acid were dissolved in 60 ml ethanol and a mixture obtained therefrom was stirred for 8 hours at a temperature of 100° C. A reaction solution obtained therefrom was cooled to ambient temperature, 3 g of sodium hydroxide dissolved in 10 mL of water was added to a filtered solution obtained from reduced filtering, and then a product obtained therefrom was extracted three times with 60 mL of water and 60 mL of dichloromethane. An organic layer obtained therefrom was dried with magnesium sulfate and solvents were evaporated therefrom to obtain residues, and the residues were separated and purified by using silica gel column chromatography to obtain 2.42 g (yield 90%) of Intermediate 2-3. The compound produced was identified by using LC-MS. C₂₀H₁₅N: M⁺ 269.1

Synthesis of Intermediate 2-4

2.69 g (10 mmol) of Intermediate 2-3 and 3.66 g (20 mmol) of 4-bromobenzaldehyde were dissolved in 10 mL of trifluoro acetic acid and then stirred in a seal tube at a temperature of 130° C. for three days. A reaction solution obtained therefrom was cooled to ambient temperature, quenched with NaHCO₃, and then a product obtained therefrom was extracted three times with 60 mL of water and 60 mL of dichloromethane. An organic layer obtained therefrom was dried with magnesium sulfate, and solvents were evaporated therefrom to obtain residues, and the residues were separated and purified by sing silica gel column chromatography to obtain 1.74 g of Intermediate 2-4 (yield 40%). The compound produced was identified by using LC-MS. Chemical Formula: C₂₇H₁₆BrN: M⁺433.1

Synthesis of Intermediate 2-5

3.37 g of Intermediate 2-5 (yield 70%) was prepared in the same manner as in the method of preparing Intermediate 2-1, except for using Intermediate 2-4 instead of 9-bromophenanthrene. The compound produced was identified by using LC-MS. C₃₃H₂₈BNO₂: M⁺481.2

Synthesis of Compound 2

4.81 g (10 mmol) of Intermediate 2-5, 2.68 g (10 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 0.58 g (0.5 mmol) of tetrakis(triphenylphosphine)palladium (Pd(PPh₃)₄), and 4.14 g (30 mmol) of K₂CO₃ were dissolved in 60 mL of a mixture solution of THF/H₂O (volume ratio of 2/1) at a temperature of 80° C. for 16 hours. A reaction solution obtained therefrom was cooled to ambient temperature, 40 mL of water was added thereto, and then a product obtained therefrom was extracted three times with 50 mL of ethyl ether. An organic layer obtained therefrom was dried with magnesium sulfate, and solvents were evaporated therefrom to obtain residues, and the residues were separated and purified by using silica gel column chromatography to obtain 3.52 g (yield 60%) of Compound 2. The compound produced was identified by using LC-MS. C₄₂H₂₆N₄: cal. 586.22, found 587.26.

¹H NMR (400 MHz, a CDCl₃) δ (ppm) 8.90 (d, 1H), 8.84 (d, 1H), 8.81-8.74 (m, 6H), 8.65 (d, 2H), 8.57 (d, 1H), 8.51 (d, 2H), 8.27 (d, 1H), 7.88-7.63 (m, 5H), 7.55-7.41 (m, 7H).

Synthesis Example 2: Synthesis of Compound 10

Synthesis of Intermediate 10-1

1.95 g (yield 45%) of Intermediate 10-1 was synthesized in the same manner as in the method of synthesizing Intermediate 2-4, except that 3-bromobenzaldehyde was used instead of 4-bromobenzaldehyde. The compound produced was identified by using LC-MS. C₂₇H₁₆BrN: M⁺433.1

Synthesis of Intermediate 10-2

3.46 g (yield 72%) of Intermediate 10-2 was synthesized in the same manner as in the method of synthesizing Intermediate 2-5, except that Intermediate 10-1 was used instead of Intermediate 2-4. The compound produced was identified by using LC-MS. C₃₃H₂₈BNO₂: M⁺481.2

Synthesis of Compound 10

4.04 g (yield 65%) of Compound 10 was synthesized in the same manner as in the method of synthesizing Compound 2, except that Intermediate 10-2 was used instead of Intermediate 2-5 and that Intermediate A was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The compound produced was identified by using LC-MS. C₄₆H₂₇N₃: cal. 621.22, found 622.32.

¹H NMR (400 MHz, a CDCl₃) δ (ppm) 8.92 (d, 1H), 8.84 (d, 1H), 8.80-8.74 (m, 2H), 8.64 (s, 1H), 8.57 (d, 1H), 8.47 (s, 1H), 8.30-8.26 (t, 2H), 8.08 (s, 1H), 7.88-7.65 (m, 9H), 7.53-7.46 (m, 6H), 7.34-7.24 (m, 2H)

Synthesis Example 3: Synthesis of Compound 16

Synthesis of Intermediate 16-1

5.04 g (15 mmol) of 3,9-dibromophenanthrene, 1.23 g (10 mmol) of pyridine-4-boronic acid, 0.58 g (0.5 mmol) of Pd(PPh₃)₄, and 4.14 g (30 mmol) of K₂CO₃ were dissolved in 60 mL of a mixture solution of THF/H₂O (volume ratio of 2/1) and then stirred at a temperature of 80° C. for 16 hours. A reaction solution obtained therefrom was cooled to ambient temperature, 40 mL of water was added thereto and then a product obtained therefrom was extracted three times with 50 mL of ethyl ether. An organic layer obtained therefrom was dried with magnesium sulfate, solvents were evaporated therefrom to obtain residues, and the residues were separated and purified by using silica gel column chromatography to obtain 3.52 g (yield 60%) of. The compound produced was identified by using LC-MS. C₁₉H₁₂BrN: M⁺333.0

Synthesis of Compound 16

3.79 g (yield 60%) of Compound 16 was synthesized in the same manner as in the method of synthesizing Compound 2, except that Intermediate 16-1 was used instead of Intermediate 2-1 and that 1-bromopyrene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The compound produced was identified by using LC-MS.

C₄₈H₂₈N₂: cal. 632.23, found 633.34.

¹H NMR (400 MHz, a CDCl₃) δ (ppm) 8.98 (s, 1H), 8.84-8.75 (m, 3H), 8.68 (s, 1H), 8.58 (d, 2H), 8.31-8.00 (m, 12H), 7.90-7.80 (m, 5H), 7.69-7.65 (m, 2H), 7.50-7.45 (m, 2H)

Synthesis Example 4: Synthesis of Compound 28

Synthesis of Intermediate 28-1

(3.70 g, 11 mmol) of 3,9-dibromophenanthrene was dissolved in 30 mL of THF to prepare a dissolution product and 4 mL of n-butyllithium (2.5 M in hexane) was added to the dissolution product at a temperature of −78° C. to prepare a mixture. After 1 hour, 2.04 ml (10 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane was added to the mixture at the same temperature. Then, the mixture was stirred at ambient temperature for 5 hours, water was added thereto, and a mixture product obtained therefrom was then washed three times with 30 mL of diethyl ether. A washed diethyl ether layer obtained therefrom was dried by using MgSO₄ and then reduced pressure dried to obtain a product, and the product was separated and purified by using silica gel column chromatography to obtain 2.47 g (yield 65%) of Intermediate 28-1 as a white solid. The compound produced was identified by using LC-MS. C₂₀H₂₀BBrO₂: M⁺382.1

Synthesis of Intermediate 28-2

3.83 g (10.0 mmol) of Intermediate 28-1, 4.04 g (20.0 mmol) of 1-bromo-2-nitrobenzene, 0.58 g (0.5 mmol) of Pd(PPh₃)₄, 0.16 g (0.5 mmol) of tetrabutylammonium bromide (TBAB), and 3.18 g (30.0 mmol) of Na₂CO₃ were dissolved in 60 mL of a mixture solution of toluene/ethanol/H₂O (volume ratio of 3/3/1), and then stirred for 16 hours at a temperature of 80° C. A reaction solution obtained therefrom was cooled to ambient temperature and then extracted three times with 60 mL of water and 60 mL of diethylether. An organic layer obtained therefrom was dried with magnesium sulfate and solvents were evaporated therefrom to obtain residues, and the residues were separated and purified by using silica gel column chromatography to obtain 2.65 g (yield 70%) of Intermediate 28-2. The compound produced was identified by using LC-MS. C₂₀H₁₂BrNO₂: M⁺377.0

Synthesis of Intermediate 28-3

3.78 g (10.0 mmol) of Intermediate 28-2, 3.56 g (30 mmol) of tin (Sn), and 5 mL (50 mmol, conc. 36.5%) of hydrochloric acid were dissolved in 60 mL ethanol and a mixture obtained therefrom was stirred for 8 hours at a temperature of 100° C. A reaction solution obtained therefrom was cooled to ambient temperature, which was then reduced-pressure filtered, 3 g of sodium hydroxide dissolved in 10 mL was added to a reduced-pressure filtered solution obtained therefrom and then extracted three times with 60 mL of water and 60 mL of dichloromethane. An organic layer obtained therefrom was dried with magnesium sulfate and solvents were evaporated therefrom to obtain residues, and the residues were separated and purified by using silica gel column chromatography to obtain 2.96 g (yield 85%) of Intermediate 28-3. The compound produced was identified by using LC-MS. C₂₀H₁₄BrN: M⁺347.0

Synthesis of Intermediate 28-4

2.69 g (10 mmol) of Intermediate 28-3 and 2.12 g (20 mmol) of benzaldehyde were dissolved in 10 mL of trifluoro acetic acid, and a dissolution product obtained therefrom was stirred in a seal tube at a temperature of 130° C. for three days. A reaction solution obtained therefrom was cooled to ambient temperature, quenched by using NaHCO₃, and then extracted three times with 60 mL of water and 60 mL of dichloromethane. An organic layer obtained therefrom was dried with magnesium sulfate and solvents were evaporated therefrom to obtain residues, and the residues were separated and purified by using silica gel column chromatography to obtain 1.74 g (yield 40%) of Intermediate 28-4. The compound produced was identified by using LC-MS. C₂₇H₁₆BrN: M⁺433.1

Synthesis of Intermediate 28-5

(4.34 g, 10 mmol) of Intermediate 28-4 was dissolved in 30 mL of THF to prepare a dissolution product and 4 mL of n-butyllithium (2.5 M in hexane) was added to the dissolution product at a temperature of −78° C. to prepare a mixture. After 1 hour, 2.04 ml (10 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane was added to the mixture at the same temperature. Then, the mixture was stirred at ambient temperature for 5 hours, water was added thereto, and then washed three times with 30 mL of diethylether. A washed diethylether layer obtained therefrom was dried by using MgSO₄ and then reduced pressure dried to obtain a product, and the product was separated and purified by using silica gel column chromatography to obtain 3.61 g (yield 75%) of Intermediate 28-5 as a white solid. The compound produced was identified by using LC-MS. C₃₃H₂₈BNO₂: M⁺481.2

Synthesis of Compound 28

4.81 g (10 mmol) of Intermediate 28-5, 3.47 g (10 mmol) of Intermediate A, 0.58 g (0.5 mmol) of Pd(PPh₃)₄, and 4.14 g (30 mmol) K₂CO₃ were dissolved in 60 mL of a mixture solution of THF/H₂O (volume ratio of 2/1) and then stirred at a temperature of 80° C. for 16 hours. A reaction solution obtained therefrom was cooled to ambient temperature, 40 mL of water was added thereto, and then extracted three times with 50 mL of ethylether. A collected organic layer was dried by using magnesium sulfate, solvents were evaporated therefrom, and residues obtained therefrom were separated and purified by using silica gel column chromatography to obtain 4.10 g (yield 66%) of Compound 28. The compound produced was identified by using LC-MS. C₄₆H₂₇N₃: cal. 621.22, found 622.32.

¹H NMR (400 MHz, a CDCl₃) δ (ppm) 8.83 (d, 1H), 8.77-8.68 (m, 3H), 8.57 (d, 1H), 8.47 (s, 1H), 8.27-8.17 (m, 3H), 7.99-7.80 (m, 5H), 7.71-7.62 (m, 6H), 7.52-7.46 (m, 5H), 7.33-7.24 (m, 2H)

Synthesis Example 5: Synthesis of Compound 32

3.62 g of Compound 32 (yield 65%) was synthesized in the same manner as in the synthesis of Compound 28, except that 2-pyridine carboxyaldehyde was used instead of benzaldehyde and 1-bromopyrene was used instead of Intermediate A. The compound produced was identified by using LC-MS. C₄₂H₂₄N₂: cal. 556.19, found 557.26.

¹H NMR (400 MHz, a CDCl₃) δ (ppm) 9.26 (d, 1H), 8.87 (d, 1H), 8.80-8.65 (m, 4H), 8.37-8.05 (m, 10H), 7.98-7.80 (4H), 7.69-7.64 (m, 2H), 7.48 (t, 1H), 7.36-7.33 (m, 1H)

Synthesis Example 6: Compound 42

3.36 g of Compound 42 (yield 63%) was synthesized in the same manner as in the synthesis of Compound 28, except that 4-formylbenzonitrile was used instead of benzaldehyde and Intermediate B was used instead of Intermediate A. The compound produced was identified by using LC-MS. C₃₉H₂₃N₃: cal. 533.19, found 534.26.

¹H NMR (400 MHz, a CDCl₃) δ (ppm) 8.87-8.70 (m, 4H), 8.60-8.54 (m, 3H), 8.36 (d, 2H), 8.27 (d, 1H), 8.06-7.79 (m, 10H), 7.66 (t, 1H), 7.50-7.42 (m, 2H)

Synthesis Example 7: Synthesis of Compound 56

Synthesis of Intermediate 56-1

3.04 g (10.0 mmol) of Intermediate 2-1, 5.622 g (20.0 mmol) of 1,4-dibromo-2-nitrobenzene, 0.58 g (0.5 mmol) of Pd(PPh₃)₄, 0.16 g (0.5 mmol) of tetrabutylammonium bromide (TBAB), and 3.18 g (30.0 mmol) of Na₂CO₃ were dissolved in 60 mL of a mixture solution of toluene/ethanol/H₂O (volume ratio of 3/3/1), and a resultant solution obtained therefrom was stirred at a temperature of 80° C. for 16 hours. A reaction solution obtained therefrom was cooled to ambient temperature and then extracted three times with 60 mL of water and 60 mL of diethylether. An organic layer obtained therefrom was dried with magnesium sulfate and solvents were evaporated therefrom to obtain residues, and the residues were separated and purified by using silica gel column chromatography to obtain 2.84 g of Intermediate 56-1 (yield 75%). The compound produced was identified by using LC-MS. C₂₀H₁₂BrNO₂: M⁺377.0

Synthesis of Intermediate 56-2

3.78 g (10.0 mmol) of Intermediate 56-1, 3.56 g (30 mmol) of tin (Sn), and 5 ml (50 mmol, conc. 36.5%) of hydrochloric acid were dissolved in 60 ml ethanol and a mixture obtained therefrom was stirred for 8 hours at a temperature of 100° C. A reaction solution obtained therefrom was cooled to ambient temperature, reduced-pressure filtered and 3 g of sodium hydroxide dissolved in 10 mL was added to a reduced-pressure filtered product obtained therefrom and then extracted three times with 60 mL of water and 60 mL of dichloromethane. An organic layer obtained therefrom was dried with magnesium sulfate and solvents were evaporated therefrom to obtain residues, and the residues were separated and purified by using silica gel column chromatography to obtain 3.13 g (yield 90%) of Intermediate 56-2. C₂₀H₁₄BrN: M⁺347.0

Synthesis of Intermediate 56-3

3.48 g (10 mmol) of Intermediate 56-2 and 2.12 (20 mmol) of benzaldehyde were dissolved in 10 mL of trifluoro acetic acid, and a dissolution product obtained therefrom was stirred in a seal tube at a temperature of 130° C. for three days. A reaction solution obtained therefrom was cooled to ambient temperature, quenched by using NaHCO₃, and then extracted three times with 60 mL of water and 60 mL of dichloromethane. An organic layer obtained therefrom was dried with magnesium sulfate and solvents were evaporated therefrom to obtain residues, and the residues were separated and purified by using silica gel column chromatography to obtain 1.74 g (yield 40%) of Intermediate 56-3. The compound produced was identified by using LC-MS. C₂₇H₁₆BrN: M⁺ 433.1

Synthesis of Intermediate 56-4

(4.34 g, 10 mmol) of Intermediate 56-3 was dissolved in 30 mL of THF to prepare a dissolution product and 4 mL of n-butyllithium (2.5 M in hexane) was added to the dissolution product at a temperature of −78° C. to prepare a mixture. After an hour, 2.04 ml (10 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane was added to the mixture at the same temperature. Then, the mixture was stirred at ambient temperature for 5 hours, water was added thereto, and then washed three times with 30 mL of diethylether. A washed diethylether layer obtained therefrom was dried by using MgSO₄ and then reduced pressure dried to obtain a product, and the product was separated and purified by using silica gel column chromatography to obtain 3.37 g (yield 70%) of Intermediate 56-4 as a white solid. The compound produced was identified by using LC-MS. C₃₃H₂₈BNO₂: M⁺481.2

Synthesis of Compound 56

4.81 g (10 mmol) of Intermediate 2-1, 2.68 g (10 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 0.58 g (0.5 mmol) of Pd(PPh₃)₄, 4.14 g (30 mmol) of K₂CO₃ were dissolved in 60 mL of a mixture solution of THF/H₂O (volume ratio of 2/1), and a resultant solution obtained therefrom was stirred at a temperature of 80° C. for 16 hours. A reaction solution obtained therefrom was cooled to ambient temperature, 40 mL of water was added thereto, and then extracted three times with 50 mL of ethylether. An organic layer obtained therefrom was dried with magnesium sulfate and solvents were evaporated therefrom to obtain residues, and the residues were separated and purified by using silica gel column chromatography to obtain 3.82 g of Compound 56 (yield 60%). The compound produced was identified by using LC-MS. C₄₂H₂₆N₄: cal. 586.22, found 587.32.

¹H NMR (400 MHz, a CDCl₃) δ (ppm) 9.16 (s, 1H), 9.05 (m, 4H), 8.81-8.74 (m, 6H), 8.02-7.97 (m, 2H), 7.83-7.60 (m, 7H), 7.54-7.41 (m, 6H)

Example 1

As an anode, a 15 Ω/cm² ITO glass substrate (1,200 Å, Corning) was cut into a size of about 50 mm×50 mm×0.7 mm, ultrasonically washed with isopropyl alcohol and pure water for 5 minutes each, irradiated with UV for 30 minutes, exposed to ozone, and then loaded onto a vacuum deposition device.

2-TNATA was deposited on the ITO anode to form an HIL having a thickness of 600 Å, NPB was deposited on the HIL to form an HTL having a thickness of 300 Å. Thereafter, ADN (host) and DPAVBi (dopant) were co-deposited on the HTL at a weight ratio of 98:2 to form an EML having a thickness of 300 Å.

Thereafter Compound 2 was deposited on the EML to form an ETL having a thickness of 300 Å, LiF was deposited on the ETL to form an EIL having a thickness of 10 Å, Al was deposited on the EIL into a thickness of 10 Å, Al was deposited on the EIL to form a cathode having a thickness of 3000 Å, to thereby manufacture an organic light-emitting device.

Example 2

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 10 was used instead of Compound 2 when forming an ETL.

Example 3

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 16 was used instead of Compound 2 when forming an ETL.

Example 4

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 28 was used instead of Compound 2 when forming an ETL.

Example 5

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 32 was used instead of Compound 2 when forming an ETL.

Example 6

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 42 was used instead of Compound 2 when forming an ETL.

Example 7

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 56 was used instead of Compound 2 when forming an ETL.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Alq₃ was used instead of Compound 2 when forming an ETL.

Comparative Example 2

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound A, below, was used instead of Compound 2 when forming an ETL.

Evaluation Example 1

Driving voltages, current densities, brightness, efficiencies, emission colors, and half-life spans of the organic light-emitting device manufactured in Examples 1 to 7 and Comparative Examples 1 and 2 were measured by using Kethley SMU 236 and spectrophotometer PR650 and results obtained therefrom are shown in Table 1. The term, “half-life span” refers to an amount of time taken for the level of brightness to reach a level that is 50% of the initial level of brightness.

TABLE 1 Driving Current Half-life voltage density Brightness Efficiency Emission (hr @ Material (V) (mA/cm²) (cd/m²) (cd/A) color 100 mA/cm²) Example 1 Compound 2 5.90 50 3,150 6.30 blue 222 hr Example 2 Compound 5.58 50 2,900 5.80 blue 265 hr 10 Example 3 Compound 5.84 50 3,240 6.48 blue 300 hr 16 Example 4 Compound 5.96 50 3,110 6.22 blue 315 hr 28 Example 5 Compound 6.21 50 3,420 6.84 blue 233 hr 32 Example 6 Compound 6.05 50 3,350 6.70 blue 251 hr 42 Example 7 Compound 5.98 50 3,050 6.10 blue 286 hr 56 Comparative Alq₃ 7.35 50 2,065 4.13 blue 145 hr Example 1 Comparative Compound A 6.12 50 2,465 4.93 blue 170 hr Example 2

According to the Table 1 above, it may be seen that driving voltages, current densities, brightness, efficiencies, emission colors, and half-life spans of the organic light-emitting devices manufactured in Examples 1 to 7 were better than those of the organic light-emitting devices manufactured in Comparative Examples 1 and 2.

As described above, according to the one or more of the above embodiments, the organic light-emitting device including the condensed cyclic compound may have low driving voltage, high efficiency, high brightness, and a long lifespan.

Example embodiments have been disclosed herein, and although specific terms are employed, they are used and are to be interpreted in a generic and descriptive sense only and not for purpose of limitation. In some instances, as would be apparent to one of ordinary skill in the art as of the filing of the present application, features, characteristics, and/or elements described in connection with a particular embodiment may be used singly or in combination with features, characteristics, and/or elements described in connection with other embodiments unless otherwise specifically indicated. Accordingly, it will be understood by those of skill in the art that various changes in form and details may be made without departing from the spirit and scope of the present invention as set forth in the following claims. 

What is claimed is:
 1. A condensed cyclic compound represented by Formula 1, below:

in Formula 1, L₁ to L₄ may be each independently selected from a substituted or unsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstituted C₃-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀ cycloalkenylene group, a substituted or unsubstituted C₃-C₁₀ heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀ arylene group, a substituted or unsubstituted C₂-C₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group; a1 to a4 may be each independently selected from 0, 1, 2 and 3; R₁ to R₄ may be each independently selected from hydrogen, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₃-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₃-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group, —P(═O)(Q₁)(Q₂), and —S(═O)₂(Q₁); R₅ to R₇ may be each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group; b5 to b7 are each independently selected from 1, 2, and 3; at least one substituent of the substituted C₃-C₁₀ cycloalkylene group, the substituted C₂-C₁₀ heterocycloalkylene group, the substituted C₃-C₁₀ cycloalkenylene group, the substituted C₂-C₁₀ heterocycloalkenylene group, the substituted C₆-C₆₀ arylene group, the substituted C₂-C₆₀ heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic hetero-condensed polycyclic group, the substituted C₁-C₆₀ alkyl group, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkyl group, the substituted C₂-C₁₀ heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₂-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group, the substituted C₂-C₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed hetero-polycyclic group may be selected from: deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed hetero-polycyclic group; C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group; a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed hetero-polycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group; and —P(═O)(Q₁₁)(Q₁₂) and —S(═O)₂(Q₁₁); wherein, Q₁, Q₂, Q₁₁ and Q₁₂ may be each independently selected from a C₆-C₆₀ aryl group, and a C₂-C₆₀ heteroaryl group, provided that i) when *-(L₁)_(a1)-R₁ in Formula 1 is a phenyl group, R₂ and R₅ are not a methyl group, ii) when *-(L₁)_(a1)-R₁ in Formula 1 is not a phenyl group, at least one of R₁ to R₇ are not hydrogen, iii) when *-(L₁)_(a1)-R₁ in Formula 1 is —P(═O)(Q₁)(Q₂), and Q₁ and Q₂ are phenyl groups, R₅ is not a methyl group, and iv) when *-(L₁)_(a1)-R₁ in Formula 1 is a phenyl group, at least one of R₂, R₃, and R₄ is not hydrogen.
 2. The condensed cyclic compound as claimed in claim 1, wherein L₁ to L₄ are each independently groups selected from: phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, ovalenylene, pyrrolylene, thiophenylene, furanylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isooxazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene, indolylene, indazolylene, purinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, carbazolylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzoimidazolylene, benzofuranylene, benzothiophenylene, isobenzothiazolylene, benzooxazolylene, isobenzooxazolylene, triazolylene, tetrazolylene, oxadiazolylene, triazinylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, and dibenzocarbazolylene; and phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, ovalenylene, pyrrolylene, thiophenylene, furanylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isooxazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene, indolylene, indazolylene, purinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, carbazolylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzoimidazolylene, benzofuranylene, benzothiophenylene, isobenzothiazolylene, benzooxazolylene, isobenzooxazolylene, triazolylene, tetrazolylene, oxadiazolylene, triazinylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene and dibenzocarbazolylene, each substituted with at least one group selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, and imidazopyridinyl.
 3. The condensed cyclic compound as claimed in claim 1, wherein L₁ to L₄ are each independently selected from groups represented by Formulae 3-1 to 3-30 below:

in Formulae 3-1 to 3-30, Y₁ is O, S, a C(Z₃)(Z₄), N(Z₅), or Si(Z₆)(Z₃); Z₁ to Z₇ are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, d1 is an integer of 1 to 4; d2 is an integer of 1 to 3; d3 is an integer of 1 to 6; d4 is an integer of 1 to 8; d5 is an integer of 1 or 2; d6 is an integer of 1 to 5; and * and *′ are binding sites to neighboring atoms.
 4. The condensed cyclic compound as claimed in claim 1, wherein L₁ to L₄ are each independently selected from groups represented by Formulae 4-1 to 4-21 below:

in Formulae 4-1 to 4-21, * and *′ are binding sites to neighboring atoms.
 5. The condensed cyclic compound as claimed in claim 1, wherein a1 to a4 are each independently selected from 0, 1, and
 2. 6. The condensed cyclic compound as claimed in claim 1, wherein a2 to a4 are
 0. 7. The condensed cyclic compound as claimed in claim 1, wherein R₁ to R₄ are each independently groups selected from: hydrogen, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, carbazolyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyi, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, a dibenzosilolyl group, benzocarbazolyl, dibenzocarbazolyl, benzoxanthenyl, —P(═O)(Q₁)(Q₂), and —S(═O)₂(Q₁), in which Q₁ and Q₂ are each independently a C₆-C₆₀ aryl group; and phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, carbazolyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, a dibenzosilolyl group, benzocarbazolyl, dibenzocarbazolyl and benzoxanthenyl, each substituted with at least one group selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀ alkyl, a C₁-C₂₀ alkoxy, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, carbazolyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, and dibenzocarbazolyl.
 8. The condensed cyclic compound as claimed in claim 1, wherein R₁ to R₄ are each independently groups selected from: hydrogen, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, chrysenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl quinolinyl, isoquinolinyl, carbazolyl, phenanthrolinyl, benzoimidazolyl, triazinyl, benzoxanthenyl, —P(═O)(Q₁)(Q₂), and —S(═O)₂(Q₁), in which Q₁ and Q₂ are each independently selected from a phenyl group and a naphthyl group; and phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, chrysenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl quinolinyl, isoquinolinyl, carbazolyl, phenanthrolinyl, benzoimidazolyl, triazinyl and benzoxanthenyl, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a nitro group, methyl, ethyl, n-propyl, tert-butyl, methoxy, ethoxy, tert-butoxy, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, carbazolyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, and dibenzocarbazolyl.
 9. The condensed cyclic compound as claimed in claim 1, wherein R₁ to R₄ are each independently selected from hydrogen, —P(═O)(Ph)₂, —S(═O)₂(Ph) and a group represented by any one of Formulae 5-1 to 5-44:

in Formulae 5-1 to 5-44, * is a binding site to a neighboring atom.
 10. The condensed cyclic compound as claimed in claim 1, wherein R₅ to R₇ are each independently groups selected from: hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, C₁-C₂₀ alkyl, C₁-C₂₀ alkoxy, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, carbazolyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, a dibenzosilolyl group, benzocarbazolyl, dibenzocarbazolyl, and benzoxanthenyl; and phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, carbazolyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, a dibenzosilolyl group, benzocarbazolyl, dibenzocarbazolyl and benzoxanthenyl, each substituted with at least one group selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, C₁-C₂₀ alkyl, C₁-C₂₀ alkoxy, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, carbazolyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, and dibenzocarbazolyl.
 11. The condensed cyclic compound as claimed in claim 1, wherein R₅ to R₇ are each independently groups selected from: hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, methyl, ethyl, n-propyl, tert-butyl, methoxy, ethoxy, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, chrysenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl quinolinyl, isoquinolinyl, carbazolyl, phenanthrolinyl, benzoimidazolyl, triazinyl, and benzoxanthenyl; and phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, chrysenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl quinolinyl, isoquinolinyl, carbazolyl, phenanthrolinyl, benzoimidazolyl, triazinyl and benzoxanthenyl, each substituted with at least one group selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a nitro group, methyl, ethyl, n-propyl, tert-butyl, methoxy, ethoxy, tert-butoxy, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, carbazolyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, and dibenzocarbazolyl.
 12. The condensed cyclic compound as claimed in claim 1, wherein R₅ to R₇ are each independently selected from hydrogen, deuterium, a cyano group, a nitro group and a group represented by any one of Formulae 5-1 to 5-44:

in Formulae 5-1 to 5-44, * is a binding site to a neighboring atom.
 13. The condensed cyclic compound as claimed in claim 1, wherein the condensed cyclic compound represented by Formula 1 is represented by any one of Formulae 1A to 1D:

in Formulae 1A to 1D, L₁ to L₄, a1 to a4, R₁ to R₇, and b5 to b7 are the same as defined with respect to Formula 1, provided that i) when *-(L₁)a₁-R₁ in Formula 1A to 1D is a phenyl group, R₂ and R₅ are not a methyl group, ii) when *-(L₁)a₁-R₁ in Formula 1A to 1D is not a phenyl group, at least one of R₁ and is to R₇ in Formula 1A, at least one of R₁, R₂, and R₅ to R₇ in Formula 1B, at least one of R₁, R₃, and R₅ to R₇ in Formula IC and at least one of R₁ and R₄ to R₆ in Formula 1D are not hydrogen, iii) when *-(L₁)_(a1)-R₁ in Formulae 1A to 1 D is —P(═O)(Q₁)(Q₂), and Q₁ and Q₂ are phenyl groups, R₅ is not a methyl group, and iv) when *-(L₁)_(a1)-R₁ in Formula 1 is a phenyl group, at least one of R₂, R₃, and R₄ is not hydrogen.
 14. The condensed cyclic compound as claimed in claim 1, wherein the condensed cyclic compound represented by Formula 1 is represented by any one of Formulae 1E to 1H:

in Formulae 1E to 1H, L₁ to L₄, a1 to a4, and R₁ to R₄ are the same as defined with respect to Formula 1, provided that i) when *-(L₁)a₁-R₁ in Formula 1F is a phenyl group, R₂ is not a methyl group, ii) when *-(L₁)a₁-R₁ in Formula 1E to 1H is not a phenyl group, R₁ in Formula 1E, at least one of R₁ and R₂ in Formula 1F, at least one of R₁ and R₃ in Formula 1 G and at least one of R₁ and R₄ in Formula 1H are not hydrogen, iii) when *-(L₁)_(a1)-R₁ in Formulae 1E to 1H is —P(═O)(Q₁)(Q₂), and Q₁ and Q₂ are phenyl groups, R₅ is not a methyl group, and iv) when *-(L₁)_(a1)-R₁ in Formula 1 is a phenyl group, at least one of R₂, R₃, and R₄ is not hydrogen.
 15. The condensed cyclic compound as claimed in claim 14, wherein: a1 is selected from 0, 1, and 2, and L₁ to L₄ are each independently selected from a group represented by any one of Formulae 4-1 to 4-21:

in Formulae 4-1 to 4-21, * and *′ are binding sites to neighboring atoms.
 16. The condensed cyclic compound as claimed in claim 14, wherein R₁ to R₄ are each independently selected from hydrogen and a group represented by any one of Formulae 5-1 to 5-44, provided that at least one of R₁ to R₄ is not hydrogen:

in Formulae 5-1 to 5-44, * is a binding site to a neighboring atom.
 17. The condensed cyclic compound as claimed in claim 1, wherein the condensed cyclic compound represented by Formula 1 is selected from Compounds 1 to 82:


18. An organic light-emitting device, comprising: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer, wherein the organic layer includes the condensed cyclic compound as claimed in claim
 1. 19. The organic light-emitting device as claimed in claim 18, wherein the organic layer further includes an electron transport region between the emission layer and the second electrode, the electron transport region including the condensed cyclic compound.
 20. The organic light-emitting device as claimed in claim 19, wherein the electron transport region includes an electron transport layer, the electron transport layer including the condensed cyclic compound.
 21. The condensed cyclic compound as claimed in claim 1, wherein: at least one of R₁ to R₄ are each independently selected from a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₃-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₃-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₁₀ aryl group, a substituted or unsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group, —P(═O)(Q₁)(Q₂), and —S(═O)₂(Q₁); or at least one of R₅ to R₇ are each independently selected from a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₁-C₆₀ arylthio group, a substituted or unsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group.
 22. The condensed cyclic compound as claimed in claim 1, wherein: a1 is selected from 1, 2, and 3; or R₁ is selected from a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₃-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₃-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —P(═O)(Q₁)(Q₂), and —S(═O)₂(Q₁). 